1. Field of the Invention
The present invention relates to a method for preparing (E3,Z5)-3,5-dodecadienyl acetate, a sex pheromone component of Brazilian apple leafminer (Bonagota cranaodes) which is an apple pest in South American countries such as Brazil and Uruguay.
2. Description of the Related Art
Brazilian apple leafminer is one of major apple pests in South American countries such as Brazil and Uruguay and damage caused thereby has become a problem in recent years. Pesticides are used for control of Brazilian apple leafminer but their effect is not sufficient. There is accordingly a demand for the development of a new control method satisfactory from the viewpoint of the global environment and human health.
It has been elucidated (C. R. Unelius, et al., Tettrahedron Lett., 37, 1505(1996)) by C. Ricard Unelius, et al., in 1996 that the sex pheromone of Brazilian apple leafminer has (E3,Z5)-3,5-dodecadienyl acetate as a main component thereof. In addition, M. D. A. Coracini, et al., has reported that (E3,Z5)-3,5-tetradecadienyl acetate is one of subsidiary components of the sex pheromone of the insect and it is therefore known that (E3,Z5)-3,5-alkadienyl acetates having conjugated double bonds which are a double bond with E configuration at the 3-position and a double bond with Z configuration at the 5-position, each counted from the terminal acetoxyl group, are effective as a sex pheromone of Brazilian apple leafminer (M. D. A. Coracini, J. Appl. Ent., 127, 427(2003)).
Protecting groups of an alcohol industrially used in a large amount typically include an acetyl group (Protecting Groups., P. J. Kocienski, Georg Thieme Verlag Stuttgart: New York, P22(1994)), a 1-ethoxyethyl group (Protecting Groups., P. J. Kocienski, Georg Thieme Verlag Stuttgart: New York, P84(1994)), and a tetrahydropyranyl group (Protecting Groups., P. J. Kocienski, Georg Thieme Verlag Stuttgart: New York, P84(1994)).